Both do it yourself workers and skilled craftsmen often experience difficulty in maintaining correct alignment of a rotary boring tool with a work surface—such as a workpiece being drilled by a hand-held power drill. For example, dill operators may also experience difficulty in determining the depth of a rotary boring instrument as it penetrates a surface that is being worked by the tool. There is a continuing need for an apparatus that helps a user maintain the correct alignment of a rotary boring tool with a work surface as well as to indicate the depth of the boring instrument or cutting tool as it penetrates the surface. The present invention and its associated specific embodiments disclose improvements to U.S. Pat. No. 7,992,311, which is incorporated by reference herein, as well as new methods and implementations for a rotary boring tool alignment and depth indication system.